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Stable Isotope-Labeled Azoloazines. Synthesis of a 13С and 15N Isotope-Enriched Derivative of Pyrazolo[5,1-c][1,2,4]Triazine –Potential Antidiabetic Agent

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Chemistry of Heterocyclic Compounds Aims and scope

A simple and selective method for introducing stable 13C and 15N isotopes into the structure of the sodium salt of 4-oxo-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine-3,8-dicarboxylic acid diethyl ester, a potential antiglycation agent, has been developed. Labeled [1,3-13C2]-malonic ester (99% 13C) was used as the 13C isotope donor. The introduction of the 15N atom was carried out using enriched sodium nitrite (98% 15N). The obtained 13C2 and 15N isotope-labeled analog of a promising antidiabetic compound of the pyrazolo- [5,1-c][1,2,4]triazine series was characterized by NMR spectroscopy and high-resolution mass spectrometry.

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This work was carried out as part of the state assignment of the Ministry of Higher Education and Science of the Russian Federation (4.6351.2017/8.9) and with the financial support of the Russian Foundation for Basic Research (grant 17-03-01029)

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Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Tatyana S. Shestakova, Oleg S. Eltsov, Yuliya А. Yakovleva, Sergey L. Deev, Vadim А. Shevyrin, Vladimir L. Rusinov, Valery N. Charushin & Oleg N. Chupakhin

  2. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    Vladimir L. Rusinov, Valery N. Charushin & Oleg N. Chupakhin

Authors
  1. Tatyana S. Shestakova
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  2. Oleg S. Eltsov
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  3. Yuliya А. Yakovleva
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  4. Sergey L. Deev
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  5. Vadim А. Shevyrin
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  6. Vladimir L. Rusinov
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  7. Valery N. Charushin
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  8. Oleg N. Chupakhin
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Corresponding author

Correspondence to Sergey L. Deev.

Additional information

Supplementary information file containing 1H and 13C NMR spectra of compound [13C2,15N]-1 is available at the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(9), 856–860

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Shestakova, T.S., Eltsov, O.S., Yakovleva, Y.А. et al. Stable Isotope-Labeled Azoloazines. Synthesis of a 13С and 15N Isotope-Enriched Derivative of Pyrazolo[5,1-c][1,2,4]Triazine –Potential Antidiabetic Agent. Chem Heterocycl Comp 55, 856–860 (2019). https://doi.org/10.1007/s10593-019-02549-8

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  • DOI: https://doi.org/10.1007/s10593-019-02549-8

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